data_393
# 
_chem_comp.id                                    393 
_chem_comp.name                                  "(5-CHLORO-2-{[(3-NITROBENZYL)AMINO]CARBONYL}PHENOXY)ACETIC ACID" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C16 H13 Cl N2 O6" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         IDD393 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     2006-10-05 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   ? 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        364.737 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     393 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        ? 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  RCSB 
# 
loop_
_chem_comp_atom.comp_id 
_chem_comp_atom.atom_id 
_chem_comp_atom.alt_atom_id 
_chem_comp_atom.type_symbol 
_chem_comp_atom.charge 
_chem_comp_atom.pdbx_align 
_chem_comp_atom.pdbx_aromatic_flag 
_chem_comp_atom.pdbx_leaving_atom_flag 
_chem_comp_atom.pdbx_stereo_config 
_chem_comp_atom.model_Cartn_x 
_chem_comp_atom.model_Cartn_y 
_chem_comp_atom.model_Cartn_z 
_chem_comp_atom.pdbx_model_Cartn_x_ideal 
_chem_comp_atom.pdbx_model_Cartn_y_ideal 
_chem_comp_atom.pdbx_model_Cartn_z_ideal 
_chem_comp_atom.pdbx_component_atom_id 
_chem_comp_atom.pdbx_component_comp_id 
_chem_comp_atom.pdbx_ordinal 
393 C1   C1   C  0  1 Y N N 16.859 -4.108  10.902 6.021 -2.546 -4.741 C1   393 1  
393 N2   N2   N  1  1 N N N 17.319 -3.200  9.949  7.031 -3.537 -4.860 N2   393 2  
393 O3   O3   O  -1 1 N N N 16.583 -2.759  9.056  8.164 -3.203 -5.282 O3   393 3  
393 O4   O4   O  0  1 N N N 18.495 -2.925  10.133 6.763 -4.721 -4.538 O4   393 4  
393 C5   C5   C  0  1 Y N N 17.722 -4.561  11.893 4.753 -2.894 -4.274 C5   393 5  
393 C6   C6   C  0  1 Y N N 17.269 -5.473  12.848 3.771 -1.917 -4.161 C6   393 6  
393 C7   C7   C  0  1 N N N 18.241 -5.950  13.936 2.406 -2.291 -3.659 C7   393 7  
393 N8   N8   N  0  1 N N N 17.577 -6.755  14.941 2.308 -2.174 -2.222 N8   393 8  
393 C9   C9   C  0  1 N N N 17.726 -8.090  14.948 1.910 -1.003 -1.568 C9   393 9  
393 C10  C10  C  0  1 Y N N 16.910 -8.959  15.872 1.885 -1.036 -0.112 C10  393 10 
393 C11  C11  C  0  1 Y N N 16.264 -10.099 15.422 0.967 -0.237 0.569  C11  393 11 
393 C12  C12  C  0  1 Y N N 15.509 -10.896 16.289 0.927 -0.255 1.963  C12  393 12 
393 C13  C13  C  0  1 Y N N 15.398 -10.547 17.641 1.806 -1.071 2.676  C13  393 13 
393 CL1  CL1  CL 0  0 N N N 14.401 -11.428 18.681 1.756 -1.092 4.396  CL1  393 14 
393 C15  C15  C  0  1 Y N N 16.046 -9.395  18.099 2.724 -1.870 1.995  C15  393 15 
393 C16  C16  C  0  1 Y N N 16.803 -8.596  17.235 2.763 -1.853 0.600  C16  393 16 
393 O17  O17  O  0  1 N N N 17.491 -7.440  17.576 3.668 -2.640 -0.047 O17  393 17 
393 C18  C18  C  0  1 N N N 16.996 -6.700  18.722 5.047 -2.409 0.235  C18  393 18 
393 C19  C19  C  0  1 N N N 15.792 -5.891  18.274 5.896 -3.349 -0.574 C19  393 19 
393 O20  O20  O  0  1 N N N 15.008 -5.444  19.231 7.211 -3.116 -0.335 O20  393 20 
393 O21  O21  O  0  1 N N N 15.515 -5.716  17.096 5.483 -4.206 -1.341 O21  393 21 
393 O22  O22  O  0  1 N N N 18.340 -8.643  14.040 1.608 0.036  -2.179 O22  393 22 
393 C23  C23  C  0  1 Y N N 15.935 -5.902  12.781 4.037 -0.598 -4.509 C23  393 23 
393 C24  C24  C  0  1 Y N N 15.079 -5.448  11.770 5.305 -0.251 -4.976 C24  393 24 
393 C25  C25  C  0  1 Y N N 15.538 -4.530  10.823 6.297 -1.225 -5.092 C25  393 25 
393 H5   H5   H  0  1 N N N 18.742 -4.208  11.924 4.533 -3.924 -3.999 H5   393 26 
393 H71  1H7  H  0  1 N N N 19.028 -6.556  13.463 1.641 -1.645 -4.103 H71  393 27 
393 H72  2H7  H  0  1 N N N 18.661 -5.062  14.432 2.157 -3.323 -3.929 H72  393 28 
393 HN8  HN8  H  0  1 N N N 17.005 -6.315  15.633 2.604 -2.974 -1.672 HN8  393 29 
393 H11  H11  H  0  1 N N N 16.345 -10.378 14.382 0.278 0.403  0.024  H11  393 30 
393 H12  H12  H  0  1 N N N 15.012 -11.780 15.916 0.206 0.373  2.481  H12  393 31 
393 H15  H15  H  0  1 N N N 15.960 -9.117  19.139 3.412 -2.508 2.543  H15  393 32 
393 H181 1H18 H  0  0 N N N 16.704 -7.397  19.521 5.285 -1.378 -0.040 H181 393 33 
393 H182 2H18 H  0  0 N N N 17.779 -6.034  19.113 5.223 -2.566 1.302  H182 393 34 
393 HO20 HO20 H  0  0 N N N 14.259 -5.003  18.847 7.790 -3.717 -0.852 HO20 393 35 
393 H23  H23  H  0  1 N N N 15.562 -6.594  13.522 3.271 0.167  -4.421 H23  393 36 
393 H24  H24  H  0  1 N N N 14.062 -5.808  11.723 5.521 0.778  -5.248 H24  393 37 
393 H25  H25  H  0  1 N N N 14.883 -4.158  10.049 7.280 -0.941 -5.458 H25  393 38 
# 
loop_
_chem_comp_bond.comp_id 
_chem_comp_bond.atom_id_1 
_chem_comp_bond.atom_id_2 
_chem_comp_bond.value_order 
_chem_comp_bond.pdbx_aromatic_flag 
_chem_comp_bond.pdbx_stereo_config 
_chem_comp_bond.pdbx_ordinal 
393 C1  N2   SING N N 1  
393 C1  C25  DOUB Y N 2  
393 C1  C5   SING Y N 3  
393 N2  O3   SING N N 4  
393 N2  O4   DOUB N N 5  
393 C5  C6   DOUB Y N 6  
393 C5  H5   SING N N 7  
393 C6  C23  SING Y N 8  
393 C6  C7   SING N N 9  
393 C7  N8   SING N N 10 
393 C7  H71  SING N N 11 
393 C7  H72  SING N N 12 
393 N8  C9   SING N N 13 
393 N8  HN8  SING N N 14 
393 C9  O22  DOUB N N 15 
393 C9  C10  SING N N 16 
393 C10 C11  DOUB Y N 17 
393 C10 C16  SING Y N 18 
393 C11 C12  SING Y N 19 
393 C11 H11  SING N N 20 
393 C12 C13  DOUB Y N 21 
393 C12 H12  SING N N 22 
393 C13 C15  SING Y N 23 
393 C13 CL1  SING N N 24 
393 C15 C16  DOUB Y N 25 
393 C15 H15  SING N N 26 
393 C16 O17  SING N N 27 
393 O17 C18  SING N N 28 
393 C18 C19  SING N N 29 
393 C18 H181 SING N N 30 
393 C18 H182 SING N N 31 
393 C19 O21  DOUB N N 32 
393 C19 O20  SING N N 33 
393 O20 HO20 SING N N 34 
393 C23 C24  DOUB Y N 35 
393 C23 H23  SING N N 36 
393 C24 C25  SING Y N 37 
393 C24 H24  SING N N 38 
393 C25 H25  SING N N 39 
# 
loop_
_pdbx_chem_comp_descriptor.comp_id 
_pdbx_chem_comp_descriptor.type 
_pdbx_chem_comp_descriptor.program 
_pdbx_chem_comp_descriptor.program_version 
_pdbx_chem_comp_descriptor.descriptor 
393 SMILES           ACDLabs              10.04 O=C(c1c(OCC(=O)O)cc(Cl)cc1)NCc2cccc([N+]([O-])=O)c2                                                                                    
393 InChI            InChI                1.02b InChI=1/C16H13ClN2O6/c17-11-4-5-13(14(7-11)25-9-15(20)21)16(22)18-8-10-2-1-3-12(6-10)19(23)24/h1-7H,8-9H2,(H,18,22)(H,20,21)/f/h18,20H 
393 InChIKey         InChI                1.02b VABIMMIJVWNHFI-CMLSCEPHCB                                                                                                              
393 SMILES_CANONICAL CACTVS               3.341 OC(=O)COc1cc(Cl)ccc1C(=O)NCc2cccc(c2)[N+]([O-])=O                                                                                      
393 SMILES           CACTVS               3.341 OC(=O)COc1cc(Cl)ccc1C(=O)NCc2cccc(c2)[N+]([O-])=O                                                                                      
393 SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 c1cc(cc(c1)[N+](=O)[O-])CNC(=O)c2ccc(cc2OCC(=O)O)Cl                                                                                    
393 SMILES           "OpenEye OEToolkits" 1.5.0 c1cc(cc(c1)[N+](=O)[O-])CNC(=O)c2ccc(cc2OCC(=O)O)Cl                                                                                    
# 
loop_
_pdbx_chem_comp_identifier.comp_id 
_pdbx_chem_comp_identifier.type 
_pdbx_chem_comp_identifier.program 
_pdbx_chem_comp_identifier.program_version 
_pdbx_chem_comp_identifier.identifier 
393 "SYSTEMATIC NAME" ACDLabs              10.04 "{5-chloro-2-[(3-nitrobenzyl)carbamoyl]phenoxy}acetic acid"           
393 "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "2-[5-chloro-2-[(3-nitrophenyl)methylcarbamoyl]phenoxy]ethanoic acid" 
# 
